Gold(I) and palladium(II) complexes of 1,3,4-trisubstituted 1,2,3-triazol-5-ylidene "click" carbenes: systematic study of the electronic and steric influence on catalytic activity

James R Wright, Paul C Young, Nigel T Lucas, Ai-Lan Lee, James D Crowley

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Abstract

The synthesis of a small family of six electronically and sterically modified 1,3,4-trisubstituted 1,2,3-triazol-5-ylidene gold(I) chloride complexes is described. Additionally, the corresponding trans-[PdBr2(iPr2-bimy)(1,3,4-trisubstituted 1,2,3-triazol-5-ylidene)] complexes are also generated and used to examine the donor strength of the 1,3,4-trisubstituted 1,2,3-triazol-5-ylidene ligands. All compounds have been characterized by (1)H and (13)C NMR and IR spectroscopy, high-resolution electrospray mass spectrometry (HR-ESI-MS), and elemental analysis. The molecular structures of four of the gold(I) and four of the palladium(II) complexes were determined using X-ray crystallography. Finally, it is demonstrated that these 1,2,3-triazol-5-ylidene gold(I) chloride complexes (Au(trz)Cl) are able to catalyze the cycloisomerization of 1,6-enynes, in high yield and regioselectivity, as well as the intermolecular direct etherification of allylic alcohols. Exploiting the Au(trz)Cl precatalysts allowed the etherification of allylic alcohols to be carried out under milder conditions, with better yield and regioselectivity than selected commercially available gold(I) catalysts.
Original languageEnglish
Pages (from-to)7065-7076
Number of pages12
JournalOrganometallics
Volume32
Issue number23
DOIs
Publication statusPublished - 9 Dec 2013

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Keywords

  • N-HETEROCYCLIC CARBENES
  • NORMAL 1,2,3-TRIAZOLYLIDENE LIGANDS
  • AZIDE-ALKYNE CYCLOADDITION
  • HOMOGENEOUS AU-CATALYSIS
  • ONE-POT SYNTHESIS
  • C MULTIPLE BONDS
  • WATER OXIDATION
  • 1,4-DISUBSTITUTED 1,2,3-TRIAZOLES
  • COPPER(I) COMPLEXES
  • MONOALLYLIC DIOLS

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